8 Flagler Dr, Rye, NY 10580
Property image
Property image
OFF MARKET

8 Flagler Dr
Rye, NY 10580

  • 6 Beds
  • 6.5 Baths
  • 9,153 sqft (on 1.62 acres)

$5,988,600

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $38,192/mo*
Refinance Your Home

$5,988,600

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $38,192/mo*
Refinance Your Home
6 Beds
6.5 Baths
9,153 sqft
(on 1.62 acres)

Home Value

Trulia Estimate
$5.99M
Since last month
Increased$83K (+1.4%)
Since last year
Increased$772K (+15%)
Since last sale
Increased$2M (+34.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +62% in the last 10 years
MonthEstimated value
2026
August 2026$5.91M
July 2026$5.83M
June 2026$5.89M
May 2026$5.7M
April 2026$5.43M
March 2026$5.46M
February 2026$5.46M
January 2026$5.48M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
73 Park Drive S, Rye, NY
0.38
Single-Family Home
$7,200,000
11/10/25
6
7
8,585
18 Lakeside Drive, Rye, NY
0.13
Single-Family Home
$3,450,000
05/29/26
5
4.5
4,612
325 Highland Road, Rye, NY
0.24
Single-Family Home
$3,950,000
09/23/25
4
5
4,687
14 Lakeside Drive, Rye, NY
0.15
Single-Family Home
$2,400,000
04/07/26
5
8
6,629
1 Polly Pk Road, RYE, NY
0.34
Single-Family Home
$2,100,000
09/26/25
5
5.5
5,789
5 Sunset Ln, Rye, NY
0.79
Single-Family Home
$8,000,000
08/25/25
7
6
8,352
26 GRISWOLD Road, Rye, NY
0.52
Single-Family Home
$4,300,000
09/10/25
5
5
6,545
19 Hilltop Place, Rye, NY
0.42
Single-Family Home
$10,750,000
10/03/25
9
10.5
11,236
17 Boxwood Lane, Rye, NY
0.93
Single-Family Home
$6,505,000
04/23/26
5
6
7,150
527 Purchase Street, Rye, NY
0.29
Single-Family Home
$2,050,000
06/03/26
4
4.5
3,895

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5 Flagler Drive, Rye, NY 10580
0.07
$3,729,400
5
7.5
6,339
Off Market
18 Lakeside Drive, Rye, NY 10580
0.13
$3,450,000
5
4.5
4,612
Recently Sold
14 Lakeside Drive, Rye, NY 10580
0.15
$2,400,000
5
8
6,629
Recently Sold
33 Mount Holly Drive, Rye, NY 10580
0.17
$3,466,000
5
4.5
5,178
Off Market
58 BROOKRIDGE Court, Rye Brook, NY 10573
0.21
$983,700
3
2.5
1,896
Off Market
7 Stonegate Lane, Rye, NY 10580
0.20
$3,225,600
4
5.5
6,069
Off Market
20 Mt. Holly, Rye, NY 10580
0.20
$1,525,000
-
-
-
For Sale
27 Brookridge Court, Rye Brook, NY 10573
0.23
$820,500
2
2.5
1,892
Off Market
25 Brookridge Court, Rye Brook, NY 10573
0.23
$839,800
2
2.5
1,692
Off Market
38 Brookridge Court #38, Pt Chester, NY 10573
0.25
$817,100
2
2.5
1,692
Off Market
15 Brookridge Court, Rye Brook, NY 10573
0.27
$739,000
2
2.5
1,892
Recently Sold
450 Purchase Street, Rye, NY 10580
0.23
$2,845,700
5
4.5
5,541
Off Market

Local Information

  • Map ViewExplore the area around 8 Flagler Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1997
Lot Size
1.62 acres
Living Area
9,153 sqft
Price/Sqft
$654
Parking
Garage

About this House

Custom-built Georgian brick Colonial located in the sought-after Flagler Matthew Estate area, just minutes from Metro North, Rye Country Day School and downtown Rye. Set on 1.62 level acres, the property features breathtaking views of the pond, soothing waterfall, manicured English gardens and rolling lawns. The first level is perfect for formal entertaining with grand entry foyer, formal living and dining rooms and English conservatory as well as comfortable everyday living in the family room, Christopher Peacock kitchen, study and sunny sitting area. The expansive patio provides a great spot for intimate outdoor dining as well as large-scale gatherings. The second level includes a stunning master suite with spa bath, sitting room with fireplace and boasting a balcony overlooking the pond and lush landscaped grounds. Four additional bedrooms with ensuite baths and a cozy second floor den complete the second level. This impressive home is not to be missed!
8 Flagler Dr, Rye, NY 10580 is a 6 bedroom, 7 bathroom, 9,153 sqft single-family home built in 1997. It last sold for $4,400,000 on Oct 27, 2017. It is currently off market. The Trulia Estimate is $5,988,600, with a rent estimate of $28,807/month.

Home Details for 8 Flagler Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Brick
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.62 acres

Price and Tax history

DateEventPrice
Oct 27, 2017
Source: OneKey® MLS as distributed by MLS GRID #H4727787
Sold
$4,400,000
Oct 19, 2017
Source: Agent Provided
Pending
$4,800,000
Jul 6, 2017
Source: Agent Provided
Listed For Sale
$4,800,000

Market trends in Rye

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.44M
Sale-to-List Price
105.3%
Price per sq ft
$743
Available listings
39
2MoM

Around this home

What Locals Say about Rye

At least 150 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there's holiday spirit

  • 81 % Say people would walk alone at night

  • 81 % Say kids play outside

  • 81 % Say yards are well-kept

  • 77 % Say car is needed

  • 77 % Say parking is easy

  • 72 % Say it's quiet

  • 71 % Say streets are well-lit

  • 69 % Say it's walkable to restaurants

  • 66 % Say there's wildlife

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say there are sidewalks

  • 57 % Say neighbors are friendly

  • 56 % Say there are community events

  • 44 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Zjstempel
    "There are a lot of good public parks and nice sidewalks to walk on. also a lot of people own their own dogs"
    0
    Flag
  • Dbenzanava
    "Dogs owners would like it very much. There are special Dog bakeries & pet shops catering to your pet. "
    0
    Flag
  • Brianrollins1959
    "When we walk our dog.There is always someone else walking their dog.Every one usually picks up after their dog "
    0
    Flag
  • Brianrollins1959
    "I get on 287 in the AM . It’s a 15 minute ride to White Plains. But when l come home at 12:30pm . Every body is stressed out. And driving on my bumper. I have to watch because they almost running into me "
    3
    Flag
  • Felix Vazquez Jr
    "They send helpful information in the mailbox which allows us to find events that are happening in the town"
    2
    Flag
  • Trulia User
    "Very kid friendly - just note it’s not the Rye school system. Nice walking area around the Neightborhood"
    1
    Flag
  • Patricia I.
    "Halloween window displays on Puchase street by the school children. Christmas street fair on Purchase st."
    1
    Flag
  • Nickalvarez4
    "7 minutes to metro north. Good parking at train station. Trains on schedule. 37 min train ride in to Grand Central."
    0
    Flag
  • Ltifdle
    "Right now my commute is down the staircase. Otherwise very convenient to all highways (i287, hutch, i95) and trains to city."
    0
    Flag
  • Ltifdle
    "Homes have large yards where it’s safe for children to play. Stores and restaurants are conveniently nearby. Easy access to major roadways and trains to city."
    0
    Flag
  • Cleary.aileen
    "I live here and it’s really a great place to live , lots of great things go on here and great community spirit "
    1
    Flag
  • Rosemary
    "Green community lots of parks great schools. Nice main avenue luxury shopping. Bistro restaurants. Some Catholic Church around. "
    0
    Flag
  • Heatherosemusic
    "Grew up here with my grandma and I love it. It’s the quintessential suburbs with proximity to Manhattan, a quaint village, great schools, a beach, an amusement park and so much more. The ideal neighborhood to raise a family. "
    6
    Flag
  • Manonbartels2008
    "Short and easy, fast commute. Plenty of trains, on time and easy access. Parking at station is hard due to permit wait list."
    1
    Flag
  • Fernando
    "I love Rye. It is a very quiet and peaceful neighborhood. the place is nice with good restaurants. "
    1
    Flag
  • Trulia User
    "Rye has Metro North station with direct access to city. Also there are 2 major highways with 4 exits in Rye."
    1
    Flag
  • Dan K.
    "Extremely safe and well kept place to live and be! Definitely a higher price point than even other parts of Westchester, but it is what it promotes itself to be. "
    1
    Flag
  • Ltifdle
    "Wonderful neighborhood to raise a family. Can walk to the club for all types of sports year-round. Many choices for great schools. Close to town, doctors, worship."
    0
    Flag
  • Michael C.
    "Extremely beautiful every season. Very quiet, family friendly to a fault. Winding roads assure privacy and security. "
    3
    Flag
  • Lriddle
    "My neighborhood is convenient to Westchester county, greenwich / Stamford by car and or nyc by train."
    0
    Flag
  • John J.
    "It’s a pretty dog friendly neighborhood. Town park with great dog community few blocks away. Few places in town have water bowls out front. I’m guessing every 3rd house has dog. "
    2
    Flag
  • Lriddle
    "Storybook Main Street with shops and restaurants. Very convenient commuting to work opportunities in Westchester, Connecticut and nyc."
    0
    Flag
  • Cchidiya
    "everything is convenient and easily accessible even by foot. it's a beautiful neighborhood. people are friendly, restaurants are organic, shopping is amazing. there is always free parking everywhere."
    0
    Flag
  • Contessa1313
    "Best of all possible areas for schools, trains, buses, walking, bicyling, water sports, gardening,etc."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 8 Flagler Dr

  • What is 8 Flagler Dr estimated to be worth?
    Trulia's estimated value for 8 Flagler Dr in Rye, NY is $5,988,600.
  • What is the price history for 8 Flagler Dr?
    8 Flagler Dr in Rye, NY last sold for $4,400,000 in October 2017.
  • Is Rye a buyer's or seller's market?
    Rye is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Rye?
    The median sale price in Rye is $2.44M.
  • Does 8 Flagler Dr have air conditioning?
    Yes, 8 Flagler Dr in Rye, NY has air conditioning.
  • Does 8 Flagler Dr have a pool?
    Yes, 8 Flagler Dr in Rye, NY has a pool.

Explore by feature - Pet Friendly

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